I think the problem is that Tk::ExecuteCommand uses a tk fileevent to watch the pipe that feedbacks from the command. Tk::fillevent on windows, only works on sockets, it will mess up on pipes.
So your options are either to switch to the IPC::Run module, or use threads.
Since windows use threads anyways, you may as well go with threads. Threads and Tk can work very well together with some precautions. See Tk-with-worker-threads for a starting point. The main precautions are to create your threads first, before any Tk code is called. Keep Tk code only in the main thread. Use shared variables to communicate between threads.
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